152 Results

32789 Homes For Sale & 32789 FL Real Estate

Home For Sale $2,825,000

Expansive aerial view showcasing the home's manicured lawn, symmetrical design, and beautiful landscaping at 1400 Place Picardy, Winter Park, FL 32789
Inviting backyard pool area with stylish outdoor seating, lush greenery, and a charming pool house at 1400 Place Picardy, Winter Park, FL 32789
Relaxing pool with lounge area, surrounded by lush greenery, perfect for outdoor entertaining at 1400 Place Picardy, Winter Park, FL 32789
On Market For 2 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4338

  • Year Built

    2008

  • $/SqFt

    $651

Fontainebleau - Don’t miss this rare opportunity to own a truly exceptional home in one of Central Florida’s most desirable communities. CORCORAN PREMIER REALTY.

Home For Sale $675,000

Inviting front entrance featuring modern stonework, elegant lighting, and a stylish glass door at 2602 Winter Park Rd, Winter Park, FL 32789
An aerial view of the home in a desirable neighborhood near a beautiful lake and lush green spaces at 2602 Winter Park Rd, Winter Park, FL 32789
An aerial view of the home highlighting the roof, backyard, and surrounding neighborhood at 2602 Winter Park Rd, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1966

  • Year Built

    1975

  • $/SqFt

    $343

Parklando - A rare blend of thoughtful design, architectural charm, and everyday convenience, all set in a storybook neighborhood that you’ll love coming home to.Schedule your private tour today. KELLER WILLIAMS ADVANTAGE III.

Home For Sale $3,288,000

Inviting front entrance with modern door, stone walkway, and lush landscaping at 731 Williams Dr, Winter Park, FL 32789
Charming home exterior showing brick pathway, front door, and well-kept landscaping at 731 Williams Dr, Winter Park, FL 32789
Bright living room with high ceilings, modern furniture, and expansive windows overlooking the backyard at 731 Williams Dr, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4260

  • Year Built

    2025

  • $/SqFt

    $772

Located within the highly desirable Dommerich Elementary, Maitland Middle, and Winter Park High School zones, and just minutes from downtown Winter Park, this home offers walkability, elegance, and convenience—wrapped into one exceptional property. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,000,000

Relaxing outdoor patio features comfortable seating, ceiling fans, and views of the pool and lush backyard at 3011 Temple Trl, Winter Park, FL 32789
Serene aerial view of home surrounded by lush greenery and lakes, with a pin marking the property location at 3011 Temple Trl, Winter Park, FL 32789
Beautiful aerial view showcases a home with solar panels, pool, a well-manicured lawn, and surrounded by lush trees at 3011 Temple Trl, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2406

  • Year Built

    1965

  • $/SqFt

    $416

Call today to schedule your tour! WEMERT GROUP REALTY LLC.

Home For Sale $495,000

Single-story home with tidy landscaping, covered entryway, and attached garage for convenience and curb appeal at 2886 Carew Ave, Winter Park, FL 32789
Inviting tiled front porch with vibrant flowers, complemented by a blue-trimmed door and adjacent window at 2886 Carew Ave, Winter Park, FL 32789
Bright living room with dark floors, showcasing a large window offering ample natural light and airy feel at 2886 Carew Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1766

  • Year Built

    1956

  • $/SqFt

    $280

Fairbanks Shores - A quiet neighborhood in the coveted Edgewater High School district, this home is just waiting to be discovered. Make your showing appointment today. OLDE TOWN BROKERS INC.

Home For Sale $2,849,000

An inviting exterior view showcasing a lush garden and stepping stone pathway at 1690 Palm Ave, Winter Park, FL 32789
A serene side view of the home with a well-maintained lawn and verdant garden at 1690 Palm Ave, Winter Park, FL 32789
Inviting entryway with a painted brick archway, a teal door, and stylish light fixtures at 1690 Palm Ave, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3967

  • Year Built

    2020

  • $/SqFt

    $718

Winter Park Heights - Amenities include: granite & quartz counter tops, Level 4 smooth finish walls & ceilings, hardwood floors in all main living areas, custom closet systems, brick paved driveway, PGT vinyl Low E insulated windows, core fill & block walls, high density spray foam insulation in ceilings, R13 in walls, Trane 16 Seer variable speed AC dual systems & 2 tankless water heaters. HOUWZER INC.

Home For Sale $2,095,000

Beautiful two-story home with manicured lawn and inviting entrance, exuding curb appeal at 1840 Bryan Ave, Winter Park, FL 32789
Inviting pool area with fountains, a fire feature, and cozy patio seating for outdoor relaxation at 1840 Bryan Ave, Winter Park, FL 32789
Serene backyard retreat featuring Adirondack chairs, artificial turf, and lush landscaping at 1840 Bryan Ave, Winter Park, FL 32789
On Market For 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3727

  • Year Built

    2014

  • $/SqFt

    $562

A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $675,000

Welcoming exterior view showcasing landscaped garden, covered porch, and vibrant curb appeal at 1399 Aloma Ave, Winter Park, FL 32789
Cozy front porch with seating, stylish lighting, and unique address plaque detail at 1399 Aloma Ave, Winter Park, FL 32789
Inviting front entrance featuring a bright red door, decorative plants, and a well-lit porch at 1399 Aloma Ave, Winter Park, FL 32789
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1804

  • Year Built

    1948

  • $/SqFt

    $374

This home is a perfect blend of classic charm and modern updates. Schedule your showing today! FLORIDA HOMES REALTY & MTG.

Home For Sale $1,400,000

Contemporary home boasts a manicured lawn, complemented by the home's sleek lines and modern landscape design at 2525 Venetian Way, Winter Park, FL 32789
Modern home featuring a statement driveway, manicured lawn and unique architectural elements at 2525 Venetian Way, Winter Park, FL 32789
Front porch with striking front door and stone accents and landscape at 2525 Venetian Way, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1993

  • Year Built

    1953

  • $/SqFt

    $702

Maitland Shores - Enjoy exclusive canal access to Lake Maitland for small watercraft in this quiet, community. KELLY PRICE & COMPANY LLC.

Home For Sale $800,000

Charming two-story home featuring brick accents and decorative black metal fence with a paved walkway at 441 N Capen Ave, Winter Park, FL 32789
Charming two-story home featuring brick accents and decorative black metal fence in a residential area at 441 N Capen Ave, Winter Park, FL 32789
Welcoming foyer with hardwood floors, stairs, and a white front door, offering a bright entrance at 441 N Capen Ave, Winter Park, FL 32789
On Market For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1745

  • Year Built

    2017

  • $/SqFt

    $458

Best value in 32789 zip code!!! Call today for your showing. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $2,295,000

Modern two-story home featuring a pool, outdoor kitchen, and large windows offering a sun-filled interior at 1760 Bryan Ave, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3005

  • Year Built

    2026

  • $/SqFt

    $764

Perfectly positioned just minutes from the boutiques, restaurants, and cultural experiences of Park Avenue, this residence captures the essence of modern living in one of Central Florida’s most coveted neighborhoods. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $2,100,000

Charming two-story home with manicured lawn, stone accents, and professionally landscaped yard at 2402.5 Temple Dr, Winter Park, FL 32789
Beautifully landscaped home with lush green lawn, elegant shrubs, and tranquil twilight view at 2402.5 Temple Dr, Winter Park, FL 32789
Inviting front porch with stone columns, manicured hedges, and stylish entryway at 2402.5 Temple Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $647

Call today for an easy showing! OLDE TOWN BROKERS INC.

Home For Sale $1,450,000

Aerial view of a well-maintained single-story home with a lush green lawn, mature trees, and a brick driveway at 2105 Fosgate Dr, Winter Park, FL 32789
Bright kitchen with stainless steel appliances, farmhouse sink, patterned backsplash, and custom vent hood at 2105 Fosgate Dr, Winter Park, FL 32789
Spacious kitchen with a large island, pendant lighting, stainless steel appliances, and custom wood accents at 2105 Fosgate Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3068

  • Year Built

    1956

  • $/SqFt

    $473

All Double Pane Aluminum Windows throughout home. LPT REALTY, LLC.

Home For Sale $699,000

Close-up of the address numbers and a decorated welcome sign on the entrance gate at 2711 Parkland Dr, Winter Park, FL 32789
A serene outdoor space with a pergola-covered walkway adorned with potted plants and flowers at 2711 Parkland Dr, Winter Park, FL 32789
Spacious living room featuring a fireplace, ceiling fan, and large window for ample natural light at 2711 Parkland Dr, Winter Park, FL 32789
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1618

  • Year Built

    1938

  • $/SqFt

    $432

Parklando - This exceptional home offers the quintessential Winter Park lifestyle in a location that combines established neighborhood character with exciting urban accessibility. CORCORAN PREMIER REALTY.

Home For Sale $1,495,000

Landscaped front yard featuring a circular driveway and mature magnolia tree providing ample shade at 1644 Hibiscus Ave, Winter Park, FL 32789
Well-maintained single-story home with a large front lawn, circular driveway, and carefully manicured landscaping at 1644 Hibiscus Ave, Winter Park, FL 32789
Exterior shot of a home showcasing a circular driveway, well-manicured lawn, and mature trees at 1644 Hibiscus Ave, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1974

  • $/SqFt

    $697

Flora Park - This is more than a home—it's an opportunity to live in one of Winter Park's most iconic neighborhoods. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,275,000

Charming single-story brick home featuring a well-manicured lawn and an attached two-car garage at 309 Park North Ct, Winter Park, FL 32789
Inviting home entrance with a decorative double door, brick pathway, and manicured landscaping at 309 Park North Ct, Winter Park, FL 32789
Spacious living room featuring neutral tile flooring, recessed lighting, and a view to the backyard at 309 Park North Ct, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3096

  • Year Built

    1968

  • $/SqFt

    $412

Schedule your private showing today and explore the possibilities! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,025,000

Well-appointed kitchen with an island, dark wood cabinetry, stainless steel appliances, and hardwood floors at 2923 Cove Trl, Winter Park, FL 32789
Spacious home office with hardwood floors, built-in shelving, and ample desk space for productivity at 2923 Cove Trl, Winter Park, FL 32789
Temperature-controlled wine cellar featuring custom shelving and storage for an extensive collection at 2923 Cove Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3377

  • Year Built

    1964

  • $/SqFt

    $304

*CLICK on Virtual tour link for 3D Walk Through. * KELLER WILLIAMS ADVANTAGE III.

Pended $975,000

Charming single story home with paver driveway, manicured lawn, and a well-maintained landscape at 1265 Park Pointe Ln, Winter Park, FL 32789
Inviting entryway featuring wood columns, a welcoming front door, and a well-kept stone walkway at 1265 Park Pointe Ln, Winter Park, FL 32789
Bright and spacious living room with hardwood floors, a ceiling fan, and an open floor plan at 1265 Park Pointe Ln, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2295

  • Year Built

    1989

  • $/SqFt

    $425

**Sellers will contribute $3,000 to a buyers closing costs with an accepted full price offer** KELLER WILLIAMS ADVANTAGE III.

Home For Sale $670,000

Coverage sheet including square footage for 3006 Northwood Blvd showing setbacks and square footage coverage at 3006 Northwood Blvd, Winter Park, FL 32789
This document details minimum setbacks allowed for the property and also lists existing setbacks at 3006 Northwood Blvd, Winter Park, FL 32789
Survey shows property lines, landscaping, and the location of the home at 3006 Northwood Blvd at 3006 Northwood Blvd, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1953

  • $/SqFt

    $388

Northwood Terrace - Enjoy walking distance to local favorites like East End Market, Kelly’s Ice Cream, Redlight Redlight, and Sushi Lola. ORLANDO HOMES GROUP LLC.

Home For Sale $1,150,000

Charming two-story home showcasing a beautifully landscaped front yard and a striking red front door at 795 W Canton Ave, Winter Park, FL 32789
Aerial view of the home featuring a well-manicured lawn and mature landscaping at 795 W Canton Ave, Winter Park, FL 32789
Charming two-story home featuring a striking red front door and professionally landscaped front yard at 795 W Canton Ave, Winter Park, FL 32789
On Market For 13 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2374

  • Year Built

    2017

  • $/SqFt

    $484

Don't miss this rare opportunity to own a modern gem in one of Central Florida’s most sought-after neighborhoods! WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $499,000

Charming home featuring a cozy front porch and well-maintained landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Fenced side yard with a grill, utility connections, and mature landscaping at 3601 Midiron Dr, Winter Park, FL 32789
Back yard with patio area, perfect for outdoor dining and relaxing at 3601 Midiron Dr, Winter Park, FL 32789
On Market For 14 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    954

  • Year Built

    1945

  • $/SqFt

    $523

Golfview - Schedule your showing and don't miss this incredible opportunity! EMPIRE NETWORK REALTY.

Home For Sale $2,575,000

Beautiful front entrance with a stone walkway, manicured landscaping, and a stylish modern door at 1795 Greenwich Ave, Winter Park, FL 32789
Bright and airy living room with a comfortable gray sectional, wood floors, and access to the outdoors at 1795 Greenwich Ave, Winter Park, FL 32789
Stylish living room showcasing a modern fireplace, comfortable seating, and large windows at 1795 Greenwich Ave, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3852

  • Year Built

    2019

  • $/SqFt

    $668

Zoned for top-rated Winter Park schools (Brookshire, Glenridge, Winter Park High) and near private schools- Lake Highland Prep, Park Maitland, Geneva School and more KELLY PRICE & COMPANY LLC.

Home For Sale $1,299,000

Beautiful home featuring a brick driveway, lush lawn, and meticulous landscaping at 1341 Lyndale Blvd, Winter Park, FL 32789
Inviting front entryway with a stylish light fixture and elegant glass-paneled door at 1341 Lyndale Blvd, Winter Park, FL 32789
Elegant hallway features hardwood floors, archways, and modern chandelier at 1341 Lyndale Blvd, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2388

  • Year Built

    2007

  • $/SqFt

    $544

Dixie Terrace - Located in a top-rated school district and are the corner from shops, restaurants, parks, and more, this home offers a lifestyle of comfort, charm, and convenience in one of Winter Park’s most sought-after neighborhoods. COMPASS FLORIDA LLC.

Home For Sale $2,295,000

An inviting backyard with a sparkling pool, jacuzzi, outdoor fireplace, and ample lounging space at 2614 Parkland Dr, Winter Park, FL 32789
A captivating aerial view showcasing the home's backyard pool, patio, and impeccable landscaping at 2614 Parkland Dr, Winter Park, FL 32789
An aerial view displays the home's beautiful landscaping, unique driveway, and a tranquil setting at 2614 Parkland Dr, Winter Park, FL 32789
On Market For 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3307

  • Year Built

    2007

  • $/SqFt

    $694

Parklando - With a brand-new tile roof, all-natural gas appliances, and an unbeatable location, this home is the definition of elevated Winter Park living. JW GASTON LLC.

Home For Sale $3,850,000

Charming two-story home with manicured lawn, gray metal roof and blue shutters at 2171 Forrest Rd, Winter Park, FL 32789
Elegant foyer with hardwood floors, a chandelier, and a wood-framed glass door at 2171 Forrest Rd, Winter Park, FL 32789
Inviting sitting room with built-in bookshelves and comfortable seating at 2171 Forrest Rd, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4565

  • Year Built

    2016

  • $/SqFt

    $843

This remarkable property offers the ultimate in refined living, combining luxury, comfort and convenience in one of Central Florida’s sought-after communities. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $3,195,000

Charming home entrance featuring a pergola with covered walkway, leading to the custom doors and lush landscaping at 1020 Mayfield Ave, Winter Park, FL 32789
Beautiful custom entryway with modern pergola and custom door design framed by manicured greenery at 1020 Mayfield Ave, Winter Park, FL 32789
Elegant front entrance with custom wood door framed by symmetrical landscaping and a neutral color palette at 1020 Mayfield Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2663

  • Year Built

    1989

  • $/SqFt

    $1,200

Kronenberger - Located just a short drive, walk, or bike ride from Park Avenue, this impeccable home is close to both Interlachen Country Club, the Winter Park Racquet Club, nearby shops and dining, Advent Health, and is zoned for the A-rated Lakemont/Maitland/WPHS school district. KELLY PRICE & COMPANY LLC.

Home For Sale $2,550,000

Reduced By $100,000

Contemporary home boasts a modern facade, two-car garage, manicured lawn, and an elegant design at 1700 Palm Ave, Winter Park, FL 32789
Aerial view of a modern home with a backyard oasis including a swimming pool, patio, and lush green lawn at 1700 Palm Ave, Winter Park, FL 32789
Outdoor kitchen featuring stainless steel appliances, marble counters, a wood ceiling, and a view of the pool at 1700 Palm Ave, Winter Park, FL 32789
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3770

  • Year Built

    2016

  • $/SqFt

    $676

Winter Park Heights - 1700 Palm Ave. delivers fabulous living in one of Central Florida’s most coveted neighborhoods. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,550,000

Scenic brick-paved street lined with mature trees draped with Spanish moss at 1661 Woodland Ave, Winter Park, FL 32789
Inviting home entrance with double doors, white chairs, and decorative brickwork at 1661 Woodland Ave, Winter Park, FL 32789
Spacious living area with hardwood floors, arched windows, a chaise lounge, and a dining table at 1661 Woodland Ave, Winter Park, FL 32789
On Market For 20 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3215

  • Year Built

    1948

  • $/SqFt

    $482

Comstock Park - This home blends elegance, comfort, and functionality—an entertainer’s dream with a fantastic flow for everyday living! FANNIE HILLMAN & ASSOCIATES.

Pended $1,795,000

Landscaped front yard featuring a modern two-story home with a two-car garage and beautiful curb appeal at 2813 Northwood Blvd, Winter Park, FL 32789
Bright foyer featuring a glass-paneled front door, hardwood floors, and modern decor at 2813 Northwood Blvd, Winter Park, FL 32789
Modern staircase with a unique hanging light fixture and natural light from a nearby window at 2813 Northwood Blvd, Winter Park, FL 32789
On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3444

  • Year Built

    2021

  • $/SqFt

    $521

Northwood Terrace - Experience the elegance and lifestyle this home offers and reach out today to arrange your private showing. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $525,000

A single-story home with a screened-in porch and a concrete driveway surrounded by mature trees at 2507 Lafayette Ave, Winter Park, FL 32789
The side of the house with an exterior door, small window and trash bins along a stone path at 2507 Lafayette Ave, Winter Park, FL 32789
The home's backyard with lush green ground cover, trees, a grill, and a ladder at 2507 Lafayette Ave, Winter Park, FL 32789
On Market For 21 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    943

  • Year Built

    1956

  • $/SqFt

    $557

Winter Park Village - Your future of luxury living in Winter Park awaits on Lafayette Avenue. -- RE/MAX ASSURED.

Home For Sale $3,490,000

Modern kitchen with marble island, sleek gray cabinetry, pendant lighting, and stainless steel appliances at 1910 Glencoe Rd, Winter Park, FL 32789
Bright living room with fireplace, custom built-ins, hardwood floors, and large windows at 1910 Glencoe Rd, Winter Park, FL 32789
Serene bedroom with a canopy bed, neutral decor, and a sliding glass door to the outdoors at 1910 Glencoe Rd, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4205

  • Year Built

    2025

  • $/SqFt

    $830

Schedule your private showing today and experience the epitome of luxury Winter Park living. COMPASS FLORIDA LLC.

Home For Sale $3,295,000

Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Close up view of the front entrance with modern design, black door and side lights at 532 Worthington Dr, Winter Park, FL 32789
Open concept Living Room includes hardwood floors, large dining table, and direct access to the patio at 532 Worthington Dr, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3974

  • Year Built

    2023

  • $/SqFt

    $829

Kenilworth Shores - You can make this home your new reality! FLORIDA ONE REAL ESTATE LLC.

Pended $360,200

Charming single-story home featuring manicured shrubs and a concrete walkway at 320 Granada Dr, Winter Park, FL 32789
Spacious living room with hardwood floors and a cozy fireplace at 320 Granada Dr, Winter Park, FL 32789
Bright living room featuring hardwood floors and several windows for natural light at 320 Granada Dr, Winter Park, FL 32789
On Market For 22 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1401

  • Year Built

    1946

  • $/SqFt

    $257

Don’t miss the opportunity to own a piece of Winter Park charm! KELLER WILLIAMS WINTER PARK.

Home For Sale $575,000

Reduced By $20,000

Landscaped front yard with mature tree, a driveway leading to a garage, and a well-maintained lawn at 1821 Goodrich Ave, Winter Park, FL 32789
Well-maintained front yard with a mature tree, a long driveway, and partial view of the cozy home at 1821 Goodrich Ave, Winter Park, FL 32789
Functional kitchen featuring bright yellow cabinetry, white appliances, and stylish tiled backsplash at 1821 Goodrich Ave, Winter Park, FL 32789
On Market For 23 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1955

  • $/SqFt

    $575

Sylvan Heights - Note: no house showings prior to entering into an acceptable contract and having access during the inspection period, as value is in the land. PREMIER SOTHEBY'S INTL. REALTY.

Pended $675,000

Stylish two-story townhouse showcasing a well-manicured yard and inviting curb appeal at 796 Mcintyre Ave, Winter Park, FL 32789
Welcoming front entryway with a decorative red door and attractive landscaping at 796 Mcintyre Ave, Winter Park, FL 32789
Quiet street view showcasing beautiful brick-paved road and mature trees at 796 Mcintyre Ave, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1910

  • Year Built

    1988

  • $/SqFt

    $353

Zoned for Audubon K-8 and Winter Park High School. Welcome home! FANNIE HILLMAN & ASSOCIATES.

Pended $500,000

Bungalow-style home featuring a screened porch, driveway, and established landscaping at 2011 Harmon Ave, Winter Park, FL 32789
Aerial view of the property showing the backyard, landscaping, and surrounding neighborhood at 2011 Harmon Ave, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1699

  • Year Built

    1925

  • $/SqFt

    $294

Lawndale - Property being sold for lot value. 100 x 140. Zoned R2. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,999,999

Reduced By $490,001

Charming two-story home with mature landscaping and a manicured lawn at 1299 Harding Street, Winter Park, FL 32789
Inviting home entrance featuring a brick path and lush, colorful landscaping at 1299 Harding Street, Winter Park, FL 32789
Backyard brick patio with dining and lounge seating surrounded by lush landscaping at 1299 Harding Street, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    3784

  • Year Built

    1951

  • $/SqFt

    $529

Kronenberger - Located just steps from the 5-acre Kraft Azalea Garden with lakefront trails and a fishing dock, and a short stroll to Park Avenue to enjoy a scenic boat tour or one of the many museums—this is a truly exceptional offering in one of Winter Park’s most sought-after enclaves. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $600,000

Reduced By $75,000

Covered carport area, offering protection from the elements and decorated with potted plants and grilling area at 3019 Northwood Blvd, Winter Park, FL 32789
Inviting entryway with classic furnishings and art, leading to the home's interior spaces at 3019 Northwood Blvd, Winter Park, FL 32789
Comfortable living area featuring retro furniture and decor, offering a cozy and inviting space at 3019 Northwood Blvd, Winter Park, FL 32789
On Market For 27 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1662

  • Year Built

    1953

  • $/SqFt

    $361

Northwood Terrace - 3/1.5 Bath with large Florida Room. 2 Car Carport. SAND DOLLAR REALTY GROUP INC.

Pended $569,000

Charming light blue single story home with a well manicured front yard and walkway to the front door at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room with beautiful parquet flooring, large sofa, ceiling fans, and dining area visible at 1368 Devon Rd, Winter Park, FL 32789
Spacious living room and dining area with beautiful parquet flooring and modern ceiling fans at 1368 Devon Rd, Winter Park, FL 32789
On Market For 26 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1642

  • Year Built

    1952

  • $/SqFt

    $347

Orwin Manor - Call for your private showing today! LPT REALTY, LLC.

Home For Sale $4,100,000

Charming home with a well-manicured lawn and a classic facade, perfect for suburban living at 1782 Pine Ave, Winter Park, FL 32789
Backyard featuring a refreshing pool, lush lawn, perfect for relaxation and entertainment at 1782 Pine Ave, Winter Park, FL 32789
Detailed floor plan showcasing spacious layout with multiple bedrooms, living areas, and garages at 1782 Pine Ave, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4782

  • Year Built

    2025

  • $/SqFt

    $857

Conwill Estates - Interlachen Golf community less than 5 min, Park Ave 10 min and restaurant and retail minutes away. Schedule your private tour today. EXP REALTY LLC.

Home For Sale $1,349,000

Spacious home featuring a three-car garage and manicured landscaping at 1077 Minnesota Ave, Winter Park, FL 32789
Three-car garage featuring white doors at 1077 Minnesota Ave, Winter Park, FL 32789
Two-story home featuring classic white siding, complemented by mature trees providing shade and natural beauty at 1077 Minnesota Ave, Winter Park, FL 32789
On Market For 28 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3046

  • Year Built

    2025

  • $/SqFt

    $443

Don’t miss your opportunity to own a statement home that offers both sophistication and lifestyle. Private tours available by appointment. SHORES REAL ESTATE.

Home For Sale $2,199,000

Charming one-story home with dormer windows, covered entryway, and manicured landscaping at 1394 Stewart St, Winter Park, FL 32789
Well-maintained single-story home with lush landscaping and mature trees on an expansive lawn at 1394 Stewart St, Winter Park, FL 32789
Spacious living room with brick fireplace, hardwood floors, and natural light at 1394 Stewart St, Winter Park, FL 32789
On Market For 29 Days
  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3907

  • Year Built

    1961

  • $/SqFt

    $563

Residents feel a deep sense of pride and belonging, while visitors are drawn to the charm and warmth that define our town. REALTY ONE GROUP INSPIRATION.

Pended $799,999

On Market For 25 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1128

  • Year Built

    1952

  • $/SqFt

    $709

Lake Forest Park - Demo cost to be included in the purchase price. BALDWIN PARK REALTY LLC.

Pended $359,000

Reduced By $16,000

Two-story tan home with a single car garage and mature shade trees at 156 Oak Grove Rd, Winter Park, FL 32789
Aerial view of a home with fenced backyard and mature trees at 156 Oak Grove Rd, Winter Park, FL 32789
Open concept Living Room with ceiling fan and tile floors at 156 Oak Grove Rd, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1995

  • $/SqFt

    $247

Don’t miss this exceptional opportunity—schedule your private showing today! EVERLANE REALTY LLC.

Pended $1,395,000

Inviting entryway showcasing a wood front door with decorative wreath, framed by trimmed hedges and a brick walkway at 1633 Pine Ave, Winter Park, FL 32789
Open-concept living area with hardwood floors, view of the kitchen, and neutral decor perfect for relaxing or entertaining at 1633 Pine Ave, Winter Park, FL 32789
Cozy bedroom with hardwood floors, natural light, and built-in bookcase with a quiet spot to read and unwind at 1633 Pine Ave, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2481

  • Year Built

    1951

  • $/SqFt

    $562

Lake Knowles Terrace - It's walking distance to Phelps Park and just a short drive to the charming shops and dining on Park Avenue. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $675,000

Inviting home exterior featuring a manicured lawn and a covered carport with a paved driveway at 843 W Swoope Ave, Winter Park, FL 32789
Inviting front entrance with manicured lawn and stone walkway leading to a stylish front door at 843 W Swoope Ave, Winter Park, FL 32789
Quaint home exterior with dark trim and convenient carport in a lush, green setting at 843 W Swoope Ave, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1232

  • Year Built

    1962

  • $/SqFt

    $548

Request your private showing today and make the move to Winter Park. COLDWELL BANKER RESIDENTIAL RE.

Pended $595,000

Inviting living room with hardwood floors, plenty of natural light, and comfortable seating, ideal for relaxation at 1230 N Denning Dr, Winter Park, FL 32789
Spacious living room featuring hardwood floors, a stylish area rug, and plenty of room for entertaining guests at 1230 N Denning Dr, Winter Park, FL 32789
Bright and airy living room with an open layout, hardwood flooring, and comfortable furnishings creating a welcoming space at 1230 N Denning Dr, Winter Park, FL 32789
On Market For 33 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    972

  • Year Built

    1952

  • $/SqFt

    $612

Dixie Terrace - The homes proximity to The Winter Park Cultural Corridor which includes Rollins College, The Morse Museum, The Scenic Boat Tour, and The Farmer’s Market make this a most sought-after location. Schedule your private showing today! FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,250,000

Beautiful two-story home with a brick driveway, lush landscaping, and classic architectural details at 266 Chase Ave, Winter Park, FL 32789
Stunning two-story white home with manicured landscaping, mature trees, and brick driveway at 266 Chase Ave, Winter Park, FL 32789
Elegant front door with sidelights and a hanging lantern, framed by manicured hedges at 266 Chase Ave, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4088

  • Year Built

    1930

  • $/SqFt

    $795

This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties. PREMIER SOTHEBY'S INTL. REALTY.

Pended $550,000

Backyard pool surrounded by a brick border and a wooden fence at 2906 Rapidan Trl, Winter Park, FL 32789
Entryway with parquet floors, decorative shuttered window, and a long hallway leading to the living areas at 2906 Rapidan Trl, Winter Park, FL 32789
Bright living room featuring a fireplace, neutral walls, and ample space at 2906 Rapidan Trl, Winter Park, FL 32789
*POTENTIAL GREAT VALUE
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2326

  • Year Built

    1965

  • $/SqFt

    $236

), Hvac 2010, Electrical - 2022 **we Are Accepting Any And All Offers Through 9am Monday April 7, 2025. *** KELLER WILLIAMS WINTER PARK.

Home For Sale $549,000

Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
Exterior view of home with mature trees, landscaping, and a gray truck in the driveway at 2464 Lotafun Ave, Winter Park, FL 32789
View of the driveway and carport, featuring a truck, trailer, and mature trees around the property at 2464 Lotafun Ave, Winter Park, FL 32789
On Market For 34 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1804

  • Year Built

    1951

  • $/SqFt

    $304

No limit for your imagination on this property. INTERNATIONAL FLORIDA PROPERTIES INC.

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 386 801 5417 and speak with one of our real estate consultants.

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